Aryloxypyridines

Abstract

Compounds of the formula ##STR1## wherein Py is a substituted or unsubstituted 2-, 3- or 4-pyridyl, N-oxidized or quaternized pyridyl group; A is a group of the formula (IIIA), (IIIB) or (IIIC) ##STR2## wherein ALK is straight or branched chain alkylene of 1 to 6 carbon atoms; R 1 is a carboxylic acid group, a group which is converted in the human body to a carboxylic acid group or acyl; R 2 , R 3 and R 4 are each hydrogen, a carboxylic acid group, a group which is converted in the human body to a carboxylic acid group, acyl, hydroxy, alkoxy, aralkoxy, aryloxy, an esterified hydroxy group, nitro, halogen or amino; May be formulated into pharmaceutical compositions useful for the treatment of hyperglycaemia by combining said compounds with a pharmaceutically acceptable non-toxic inert diluent or carrier. Compounds of the formula ##STR3## wherein Py is a substituted or unsubstituted 2-, 3- or 4-pyridyl, N-oxidized or quaternized pyridyl group; A is a group of formula (IIIA), (IIIB) or (IIIC) ##STR4## wherein ALK is straight or branched chain alkylene of 1 to 6 carbon atoms; R 1 is a carboxylic acid group, a group which is converted in the human body to a carboxylic acid group or acyl; R 2 , r 3 and R 4 are each hydrogen, a carboxylic acid group, a group which is converted in the human body to a carboxylic acid group, hydroxy, alkoxy, aralkoxy, aryloxy, an esterified hydroxy group, nitro, halogen, or amino, Provided that R 1 is not methyl, cyano or methoxycarbonyl when Py is 2-pyridyl or 5-ethylpyrid-2-yl and A is [O--CH 2 ]and R 2 , R 3 and R 4 are hydrogen or halogen, Are novel compounds per se. The compounds and compositions above described are useful for their hypoglycaemic activity and are useful in the treatment of hypoglycaemic conditions such as diabetes milletus.

We claim: 
     
       1. A compound of the formula ##STR21## or a pharmaceutically acceptable non-toxic acid addition salt thereof, wherein Py is 3- or 4-pyridyl unsubstituted or meta- or para-lower alkyl substituted A is [ALK-O] or [ALK-O-ALK] wherein ALK is straight or branched chain alkylene of 1 to 6 carbon atoms, only one of R a  and R b  is hydrogen and the other is selected from the group consisting of carboxy, carboloweralkoxy, cyano and carbamyl. 
     
     
       2. A compound of claim 1 wherein ALK is of 1 of 3 carbon atoms. 
     
     
       3. The compound 4-β-carboxyethylenephenoxy-2'-pyridylmethane or a pharmaceutically acceptable non-toxic acid addition salt thereof. 
     
     
       4. The compound 4-carbamylphenoxy-3'-pyridylmethane or a pharmaceutically acceptable non-toxic acid addition salt thereof. 
     
     
       5. The compound 3-(6-methyl)-pyridoxy-4'-carboxyethylphenylmethane. 
     
     
       6. The compound 3-(6-methyl)-pyridoxy-4'-methylphenylmethane. 
     
     
       7. The compound 3-carboxyethyl-phenoxy-4'pyridylmethane. 
     
     
       8. A compound according to claim 1 wherein Py is 3- or 4-pyridyl, meta- or para-lower alkyl substituted.